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Showing Compound beta-Cubebene (FDB004832)

Record Information
Version1.0
Creation date2010-04-08 22:06:25 UTC
Update date2019-11-26 03:00:15 UTC
Primary IDFDB004832
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Cubebene
DescriptionBeta-cubebene, also known as (-)-B-cubebene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Beta-cubebene is a citrus and fruity tasting compound and can be found in a number of food items such as sweet basil, roman camomile, pot marjoram, and sweet bay, which makes beta-cubebene a potential biomarker for the consumption of these food products. Beta-cubebene can be found primarily in saliva. Piper cubeba, cubeb or tailed pepper is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached – the "tails" in "tailed pepper". The dried pericarp is wrinkled, and its color ranges from grayish brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic and the taste as pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper .
CAS Number13744-15-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(-)-beta-CubebeneChEBI
(3AS-(3aalpha,3bbata,4beta,7alpha,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneChEBI
(-)-b-CubebeneGenerator
(-)-Β-cubebeneGenerator
(3AS-(3aalpha,3bbata,4b,7a,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneGenerator
(3AS-(3aalpha,3bbata,4β,7α,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneGenerator
b-CubebeneGenerator
Β-cubebeneGenerator
(3AS-(3aalpha,3bbata,4b,7a,7aa*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneHMDB
(3AS-(3aalpha,3bbata,4S,7R,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1H-cyclopenta(1,3)cyclopropa(1,2)benzeneHMDB
β-cubebenebiospider
β-cuvebenebiospider
6-epi-beta-Cubebenebiospider
beta-Cubebenebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP3.49ALOGPS
logP4.15ChemAxon
logS-4.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.7 m³·mol⁻¹ChemAxon
Polarizability26.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24
IUPAC name(1R,5S,6R,7S,10R)-10-methyl-4-methylidene-7-(propan-2-yl)tricyclo[4.4.0.0¹,⁵]decane
InChI IdentifierInChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14-,15+/m1/s1
InChI KeyFSRZGYRCMPZNJF-KHMAMNHCSA-N
Isomeric SMILESCC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSbeta-Cubebene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01rm-2900000000-dbacb878626acfeae4abSpectrum
Predicted GC-MSbeta-Cubebene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1390000000-6a944b8e46ab50de22202016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5940000000-af588cea8e1fb3c0a9d02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-9500000000-f65be015faf4afb50b4f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7e9c1e42af69f59fea702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-79206d02912ecd5353d42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1910000000-9155330998fee11bfb192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-5590000000-3e03bee8035f33df34002021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9350000000-d48bf4c96f38a991dc202021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0dac7d29bf1b8eb1d6a92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09648
Pubchem Compound ID93081
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDBETA-CUBEBENE
BIGG IDNot Available
KNApSAcK IDC00003121
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID13744-15-5
GoodScent IDrw1454791
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
citrus
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruit
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).